Shared Brunch Sail Experience

Starting at $199 pp

Rate $199 per person Description Whether you’re celebrating a school break, special family time, or just looking for an adventure on the water, come on aboard!  Kick back and enjoy a delectable brunch while taking in the sun and sea with a unique vantage point of St. Augustine on board our luxury ...

St Augustine
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Drinks, Food, Food Tour, Rentals, Sailing, Transport, Wine
St Augustine Sailing
Copy to Clipboard to Share

Shared Day Sailing Charter

Starting at $179 pp

Description Let us make your vacation complete with a 2 hour small group aboard a cozy sailboat. Enjoy the breathtaking view, feel the wind in your hair and the ocean breeze on your skin as you take in St Augustine landmarks like the Castillo de San Marco, the Bridge of Lions, and the St Augustine Lighthouse. ...

St Augustine
Boat Rental, Boat Tour, Dinner Boat, Dolphin, Eco Tour, Food Tour, Rentals, Sailing, Transportation, Water Activities, Wine
St Augustine Sailing
Copy to Clipboard to Share

Shared Sunset Sailing Charter

Starting at $179 pp

Description Make it a night to remember with a 2 hour small group sunset sail and enjoy the breathtaking view. Feel the wind in your hair and the ocean breeze caress your skin as you take in St Augustine landmarks like the Castillo de San Marco, the Bridge of Lions, and the St Augustine Lighthouse. Let ...

St Augustine
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Eco Tour, Food Tour, Rentals, Sailing, Water Activities, Wine
St Augustine Sailing
Copy to Clipboard to Share

Sip & Sail

Starting at $179 pp - Adults 21yrs +

Rate Starting at $149.00 pp for 1 hour Description Friends come together to spend a morning, afternoon or evening sipping and enjoying the sights of St. Augustine from the sea onboard a luxury sailing yacht! Your captain will ensure you and your friends enjoy your sail around the beautiful Ancient City ...

St Augustine
Boat Tour, Sailing
St Augustine Sailing
Copy to Clipboard to Share

Sunset Tasting Cruise

Starting at $349 pp

Set sail on a luxurious 2-hour Sunset Tasting Cruise with St. Augustine Sailing, where gourmet cuisine and fine wines meet breathtaking coastal views. This exclusive experience includes a sommelier-curated wine flight paired with seasonally inspired appetizers, all served as the sun sets over the water. ...

St Augustine
2 - Hours
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Food Tour, Rentals, Sailing, Sports, Water Activities, Wildlife, Wine
St Augustine Sailing
Copy to Clipboard to Share

Dolphin Delight & Nature's Wonders

Starting at $179 pp

Imagine gliding silently through the sparkling waters off the coast of St. Augustine, the sails full and the sun warm on your face. Around you, dolphins leap and play alongside the hull, their sleek forms slicing through the water as if welcoming you to their home. Overhead, pelicans dive and ospreys ...

St Augustine
2 Hours
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Eco Tour, Food Tour, Photography Tour, Sailing, Water Activities, Wildlife, Wine
St Augustine Sailing
Copy to Clipboard to Share

Shared - Sunset Dinner Cruise

Starting at $549 pp

Experience the most unique dinner setting that our Ancient City has to offer aboard our luxury sailing yacht. You and your guests will have a reserved front-row seat on the water to view the St Augustine bayfront as the sun dips behind the city. This 3 – Hour Charter Experience will include a fabulous ...

St Augustine
3
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Drinks, Food, Food Tour, Photography Tour, Rentals, Sailing, Transport, Water Activities
St Augustine Sailing
Copy to Clipboard to Share

Private Luxury Brunch Sail - Family Style

Starting at $1,500 for up to 4

Rate $1,500 up to 4 guests $149 per person for guest 5 - 10 Description Whether you’re celebrating a school break, special family time, or just looking for a fun adventure on the water - come on aboard!  Kick back and enjoy a delectable brunch while taking in the sun and sea with a unique vantage ...

St Augustine
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Eco Tour, Food Tour, Rentals, Sailing, Sports, Water Activities, Wildlife, Wine
St Augustine Sailing
Copy to Clipboard to Share

Private Day Sail Along Historic Bayfront

Starting at $595.00

Description We invite you to sit back, relax and enjoy the beautiful view and wildlife as we slip away from the dock and sail down the Tolomato River.  Make sure to look for dolphins as we approach Porpoise Point as we often see a lot of wildlife in this area.  As we continue our sail down the Matanzas ...

St Augustine
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Food Tour, Rentals, Sailing, Sports, Water Activities, Wildlife, Wine
St Augustine Sailing
Copy to Clipboard to Share

Private Sunset Sail Along Historic Bayfront

Starting at $595.00

Description Make it a night to remember with a 2 hour sunset sail aboard a luxury yacht and enjoy the breathtaking view of historic St Augustine bayfront. Feel the wind in your hair and the ocean breeze caress your skin as you take in St Augustine landmarks like the Castillo de San Marco, the Bridge ...

St Augustine
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Eco Tour, Food Tour, Rentals, Sailing, Sports, Water Activities, Wine
St Augustine Sailing
Copy to Clipboard to Share

Private Sunset Dinner Cruise

Starting at $1,995 for 2

Experience the most unique dinner setting that our Ancient City has to offer aboard our luxury sailing yacht. You and your guests will have a reserved front-row seat on the water to view the St Augustine bayfront as the sun dips behind the city. This 3 – Hour Charter Experience will include a fabulous ...

St Augustine
2
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Rentals, Sailing, Water Activities, Wildlife, Wine
St Augustine Sailing
Copy to Clipboard to Share

Sweetheart - Puppy Love Package

1 Hour - Starting at $995.00

Sweetheart - Puppy Love Experience Description Are you ready to pop the question or just looking for a one-of-a-kind date for the special someone? Either way, bring your significant other to experience the most unique setting that our Ancient City has to offer aboard a private luxury sailing yacht. As ...

St Augustine
Private Tours
Boat Rental, Boat Tour, Catamaran, Dinner Boat, Dolphin, Eco Tour, Food Tour, Rentals, Sailing, Sports, Water Activities, Wine
St Augustine Sailing
Copy to Clipboard to Share

Sailing Course Study Materials

Welcome to St Augustine Sailing's Online Store! Discover a comprehensive selection of ASA (American Sailing Association) and USCG (United States Coast Guard) study materials designed to help you master the art of sailing and navigate the waters with confidence. In addition to the above, St Augustine ...

St Augustine
Sailing
St Augustine Sailing
Copy to Clipboard to Share

Basic Keelboat Prep Class

Starting at $295 pp | 3 Hours

Set sail on your journey to becoming a confident sailor with the Basic Keelboat Prep Class! This comprehensive 3-hour course combines classroom learning and dockside instruction to build a strong foundation in sailing. Perfect for beginners, the course focuses on essential sailing vocabulary, safety ...

St Augustine
3 hours
Boat Rental, Catamaran, Lesson, Sailing, Water Activities, Workshop
St Augustine Sailing
Copy to Clipboard to Share

Intro To Sailing

Maximum of 6 people

Rates Person - $199+ Minimum of 2 guests to depart Duration 2 Hours (9AM /11AM /1PM / 3PM) Description If you've ever wanted to give sailing a try, but didn't know where to start, this is the opportunity you've been looking for.  With just a minimum of two people, we can introduce you ...

St Augustine
Boat Rental, Catamaran, Sailing, Water Activities, Workshop
St Augustine Sailing
Copy to Clipboard to Share

ASA 101 - Basic Keelboat Sailing

Starting at $1,095 | Two Day Course

Rates • Person - $1,095 Duration Two Day Course - Runs 9am to 5pm on consecutive days. About This two day course is the perfect introduction to sailing, or a good refresher if your docksiders are a bit dusty. Able to skipper a sloop-rigged keelboat of approximately 20 to 27 feet in length by day in ...

St Augustine
Boat Rental, Lesson, Sailing, Sports, Water Activities, Workshop
St Augustine Sailing
Copy to Clipboard to Share

ASA 102 - Basic Keelboat Sailing

Starting at $1,095 | Two Day Course

Rates • Person - $1,095 Duration Two Day Course - Runs 9am to 5pm on consecutive days. About This two day course is the perfect introduction to sailing, or a good refresher if your docksiders are a bit dusty. Able to skipper a sloop-rigged keelboat of approximately 20 to 27 feet in length by day in ...

St Augustine
St Augustine Sailing
Copy to Clipboard to Share

ASA 103 - Basic Coastal Cruising

Starting at $1,095 | Two Day Course

Rates • Person - $1,095 Duration Two Day Course - Runs 9am to 5pm on consecutive days. PREREQUISITES: ASA 101 About This two day course expands on the Basic Keelboat class, with an emphasis on safety and seamanship while piloting an auxiliary-powered catamaran in fair to moderate conditions in and ...

St Augustine
Sailing
St Augustine Sailing
Copy to Clipboard to Share

ASA 104 - Bareboat Cruising

Starting at $1,095 Two Day Course

Rates • Person - $1,095 Duration Two Day Course - Runs 9am to 5pm on consecutive days. PREREQUISITES: ASA 101 / ASA 103 About Able to skipper a sloop-rigged, auxiliary powered keelboat of approximately 30 to 45 feet in length during a multi-day cruise upon inland or coastal waters in moderate to heavy ...

St Augustine
Sailing
St Augustine Sailing
Copy to Clipboard to Share

ASA 105 - Coastal Navigation

ONLINE COURSE

Rate $750 - ALL FUNDS ARE NON-REFUNDABLE Class Dates This is a self paced online course. The course will be available to you for up to 120 days from the date of purchase. Description The ASA 105 Coastal Navigation online course equips students with the knowledge and skills to apply navigational theory ...

St Augustine
Sailing
St Augustine Sailing
Copy to Clipboard to Share